Dimethyl Sulfoxide → HCID 86628531, compound

Participants

Reaction Steps

A 0.30 ml portion of DMSO was dissolved in 5 ml of dichloromethane, and 0.18 ml of oxalyl chloride was added thereto while keeping the internal temperature at −60° C. or less. After 30 minutes of stirring, a dichloromethane solution (5 ml) of 323 mg of benzyl 6-{(3R,4S)-3-(hydroxymethyl)-4-[3-(trifluoromethyl)phenyl]pyrrolidin-1-yl}-6-oxohexanoate was added thereto while keeping the internal temperature at −60° C. or less, successively stirring this for 30 minutes. The reaction solution was mixed with 0.87 ml of triethylamine while keeping the internal temperature at −50° C. or less, and then stirred at −78° C. for 4.5 hours. Thereafter, work-up was carried out in the standard method to obtain benzyl 6-{(3R,4S)-3-formyl-4-[3-(trifluoromethyl)phenyl]pyrrolidin-1-yl}-6-oxohexanoate as a crude product. A mixture of the thus obtained crude product, 143 mg of (R)-(+)-1-(1-naphthyl)ethylamine, acetic acid and 5 ml of 1,2-dichloroethane was stirred for 20 minutes, and then mixed with 443 mg of sodium triacetoxyborohydride at room temperature and stirred at room temperature for 17Hours, successively carrying out work-up and purification in the standard method to obtain 312 mg of benzyl 6-{(3S,4S)-3-({[(1R)-1-(naphthyl)ethyl]amino}methyl)-4-[3-(trifluoromethyl)phenyl]pyrrolidin-1-yl}-6-oxohexanoate.

Provenance & Evidence